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Sulfuryl chloride → ethyl 5-bromo-3-chloro-1H-indole-2-carboxylate

HRID 646134
Notes
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Reaction equation

HRID 646134 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Br:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].S(Cl)([Cl:19])(=O)=O.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[Cl:19])=[CH:12][C:11]([Br:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 259091Ethyl 5-Bromoindole-2-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 28330549ethyl 5-bromo-3-chloro-1H-indole-2-carboxylateYield 85.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromoindole-2-carboxylic acid ethyl ester (4.00 g, 14.9 mmol), sulfurylchloride (1.8 mL, 22.4 mmol) and benzene (125 mL) was stirred at 90° C. for 2.5 h. The mixture was cooled to room temperature, NaHCO3 (aq., sat.) was added and the mixture extracted with EtOAc. The combined extracts were washed with water, brine and dried over Na2SO4. Concentration and recrystallisation (from toluene) gave the sub-title compound (3.87 g 85%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe mixture extracted with EtOAc
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration and recrystallisation (from toluene)

Sources & evidence

ORD record
ord-c74f13d42db74672aa0be2dd38094c51
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07705023B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes